Anthraquinone acridones.



' UNITED STATES PATENT OFFICE.

10 Drawing.

ARTHUR L'U'TTRINGHAUS, OF MANNHEIM, AND.WILHELM' B RARENQ- OF monwms HAIEN-ON-THE-RHINE, GERMANY, ASSIGNORS' TO BADISCHE ANII ILIN & SODA FABBIK OF LUDWIGSHAFEN-0N-TI-IE-RHINE, GERMANY, A CORPORATION.

ANTHRAQUINONE ACRIDONES.

Specification of Letters Patent.

Application filed September 21, 1911. Serial N0. 650,645.

To all whom it may concern:

.Be it known that We; ARTHUR Ltrrrnmcvented new and useful Improvements in Anthraquinone Acridones, of which the fol- HAUS and WILHELM BRAREN, subjects, re- [lowing is'a specification.

spectively, of the King of Prussia, residing, respectively, at Mannheim and Ludwrgshafen-on-the-Rhine, Germany, have in- 4 Our invention relates to the production of coloring matters of the anthraquinone series possessing a constitution corresponding to 20 tion agent in such a manner that an acridone ring is formed and also the second carboxylic acid group enters into reaction, so

that a second anthraquinone complex is formed. The production of our new coloring matter from 3 amino 4 methyl diphenyl-ketone-2-carboxylic acid and lchlor-anthraquinone-2-carboxylic acid takes place in steps in the manner illustrated by I the following formulae- Patented J uly 8, 1913.

Analogous formulae represent the production of the chlorinated coloring matter.

Our new coloring matters consist, when dry, of from reddish brown to yellow-brown powders which are difficultly soluble in the ordinary organic solvents. They yield deep violet vats with alkaline hydrosulfite solution and dye cotton from reddish orange to yellowish orange shades of excellent fastness. I

The following example will serve to illustrate further the nature of our invention and how it can be carried into practical effect, but the invention is not confined to this example. The parts are by Wei ht. Boil together for seven hours, in a re ux apparatus, seventy-six and a half parts of 3 amino l methyl diphenyl-l etone-2-carboxylic acid, eighty-six parts of l-chloranthraquinoneQ-carboxylic acid, three parts of copper powder, one hundred and fifty parts of calcined sodium carbonate, thirtysix parts of sodium bicarbonate, and seven hundred and fifty parts of-wa'ter. Then dilute the mixture with hot water, filter, and acidity with acetic acid, whereupon the condensation product represented by the formula l i l l is precipitated and can be purified by extracting it with boiling dilute hydrochloric acid. It is a violet powder which yields a red-violet solution-in alkali and, on the addition of hydrosulfite solution, turns light brown-red. It yields a brownish yellow solution in concentrated sulfuric acid. Then is obtained. This yields a red-violet solution in alkali and, on the addition of hydro-.

sulfite, gives the characteristic deep violet color of the anthraquinone-acridones. The formation of the second anthraquin'one residue can be caused by heating the product with sulfuric acid at about one hundredand seventy degrees centigrade until a test portion'is no longer Soluble in alkalis. The reaction product can be isolated by pouring the mixture into water and is, when dry, a reddish brown powder which is very diflicultly soluble in most organic solvents. It yields, with alkaline hydrosulfite,

a deep violet vat and colors cotton brownish heat together, for four hours, on the waterbath, ten parts of this product and one hundred parts of concentrated sulfuric acid, and pour the reaction product into water, whereupon a compound corresponding to the .formula shades which, upon oxidation in the air or, more quickly,.'by treatment witlr suitable oxidizing agents, become brilliant redorange shades of excellent fastness. In a similar manner coloring matter can be ob tained from 1 ch'lor-anthraglliinone 2-carboxylic acid and 3-amino-4- lor-diphenylketo'ne-2'-carboxylic acid, this coloring matter containing chlorin as. a substituent instead of methyl in the ortho position to the imino group of the acridin ring; and the chlorin and methyl are equivalent substituents for this purpose.

Now what we claim is 1. As new articles of manufacture the coloring matters being acridones of the ananthraquinone series and possessing a' conthraquinone series possessing a constitution 'stltution corresponding to the formula corresponding to the formula co C0 l O I xo A0 10 /xo/\lH/ c0 p N l 00 t i GIL/\T 00 i 15 X which coloring matter consists, when dry,

of a reddish brown powder which is 'difii cultly soluble in the ordinary organic soln which X n tes a S st in the vents, and which yields a deep violet shade ortho position to the imino group of the with alkaline hydrosulfite solution and dyes 2o acridin ring, which coloring matters consist, tt from a, vat reddish orange shades of when dry, of from reddish brown to yellowxmallent fa tness. brown powders which are diflicultly soluble In testimony whereof we have hereunto in the ordinary organic solvents, and which t o h nd in the presence of two subyield deep violet shades with alkaline hydro scribing witnesses.

sulfite solution and dye cotton from reddish ARTHUR LUTTRINGI-IAUS.

orange to yellowish orange shades of exeel- WILHELM BRAREN. lent fastness- Witnesses: 2. Asa new article of manufacture the J. Ame. LLOYD, coloring matter being an acridone of the JOSEPH Frame.

It is hereby certified that in Letters Patent No. 1,067,046, granted July 8, 1913, upon'the application of Arthur Luttrin'ghaus, of Mannheim, and Wilhelm Braren, of Idudwigshafen-on-the-Rhine, Germany, for an improvement in Anthraquinone Acrrdones, errors appear in the printed specification requiring correction as follows: Page 1, line 17, for the numeral 12' read 2?; page 2, line 67, for the word acridin read acrz'done; and page 3, second column, formula, for

I I 00 read v v \(io I I i Psi Wk I Gin/WV and that the said Letters Patefit should be read with these corrections therein that the same may conform to the record of the case in thetPatent Off ce-1' Sag-nod and sealed this 30th day of September, A; D., 1913. i I

\ {ma 1' l 4 v R T. ERAZ'IER,

Acting Commissioner of Paten ta.

il'oirrections in Letters Patent No. 1,067,046.

coloring matters being acridones of the ananthraquinone series and possessing a' conthraquinone series possessing a constitution 'stltution corresponding to the formula corresponding to the formula co C0 l O I xo A0 10 /xo/\lH/ c0 p N l 00 t i GIL/\T 00 i 15 X which coloring matter consists, when dry,

of a reddish brown powder which is 'difii cultly soluble in the ordinary organic soln which X n tes a S st in the vents, and which yields a deep violet shade ortho position to the imino group of the with alkaline hydrosulfite solution and dyes 2o acridin ring, which coloring matters consist, tt from a, vat reddish orange shades of when dry, of from reddish brown to yellowxmallent fa tness. brown powders which are diflicultly soluble In testimony whereof we have hereunto in the ordinary organic solvents, and which t o h nd in the presence of two subyield deep violet shades with alkaline hydro scribing witnesses.

sulfite solution and dye cotton from reddish ARTHUR LUTTRINGI-IAUS.

orange to yellowish orange shades of exeel- WILHELM BRAREN. lent fastness- Witnesses: 2. Asa new article of manufacture the J. Ame. LLOYD, coloring matter being an acridone of the JOSEPH Frame.

It is hereby certified that in Letters Patent No. 1,067,046, granted July 8, 1913, upon'the application of Arthur Luttrin'ghaus, of Mannheim, and Wilhelm Braren, of Idudwigshafen-on-the-Rhine, Germany, for an improvement in Anthraquinone Acrrdones, errors appear in the printed specification requiring correction as follows: Page 1, line 17, for the numeral 12' read 2?; page 2, line 67, for the word acridin read acrz'done; and page 3, second column, formula, for

I I 00 read v v \(io I I i Psi Wk I Gin/WV and that the said Letters Patefit should be read with these corrections therein that the same may conform to the record of the case in thetPatent Off ce-1' Sag-nod and sealed this 30th day of September, A; D., 1913. i I

\ {ma 1' l 4 v R T. ERAZ'IER,

Acting Commissioner of Paten ta.

il'oirrections in Letters Patent No. 1,067,046. 

